Asymmetric Diels-Alder reaction using a new chiral β-nitroacrylate for enantiopure trans-β-norbornane amino acid preparation

被引：9
作者：
Calmes, Monique [1 ]
Escale, Francoise [1 ]
Didierjean, Claude
Cazals, Guillaume [1 ]
Martinez, Jean [1 ,2 ]
机构：
[1] Univ Montpellier 2, CNRS, Inst Biomol Max Mousseron, UMR 5247, F-34095 Montpellier, France
[2] CNRS, Lab Cristallographie Modelisat Mat Min Biol, UMR UHP 8036, F-54506 Nancy, France
来源：
TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 20期
关键词：
D O I：
10.1016/j.tetasy.2007.10.001
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The main nitronorbornene adduct derived from the asymmetric Diels-Alder reaction of (S)-benzyl-4-(3-(3-nitroacryloyloxy)-4,4- dimethyl-2-oxopyrrolidin-1-yl) benzoate (S)-1 and cyclopentadiene was isolated and transformed to afford the enantiopure bicyclic beta-amino acid (1S,2R,3R,4R)-trans-beta-norbornane amino acid 9. The enantiomer (1R,2S,3S,4S)-9 could be obtained by the same synthetic route by using the chiral auxiliary (R)-1. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2491 / 2496
页数：6
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